Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/56—Ring systems containing three or more rings
  • C07D209/80—[b, c]- or [b, d]-condensed
  • C07D209/82—Carbazoles; Hydrogenated carbazoles
  • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system

Definitions

• the invention relates to a process for the preparation of 2-hydroxycarbazoles.
• R 2 represents halogen
• a possible optionally substituted alkyl radical (R 1 ) is a straight-chain or branched radical with up to 8, preferably with up to 4, carbon atoms. Examples which may be mentioned are the following alkyl radicals: methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl and tert.-butyl.
• a possible optionally substituted aryl radical (R 1 ) is a carbocyclic aromatic ring with 6 to 12 carbon atoms. Examples which may be mentioned are the following aryl radicals: phenyl, 2-methylphenyl, 4-methylphenyl and naphthyl, the phenyl radical being particularly preferred.
• a possible optionally substituted alkoxy radical (R 1 ) is an alkoxy radical which has a straight-chain or branched aliphatic hydrocarbon radical with up to 8, preferably 4, carbon atoms.
• alkoxy radicals which may be mentioned are: methoxy, ethoxy, propoxy and butoxy.
• halogens R 2
• fluorine chlorine and bromine
• chlorine and bromine being particularly preferred.
• Preferred compounds of the formula (II) are diphenylamines of the formula ##STR5## wherein R 1 represents hydrogen and
• R 2 represents chlorine or bromine.
• diphenylamines may be mentioned as examples: 2-chloro-3'-hydroxydiphenylamine, 2,4-dichloro-3'-hydroxydiphenylamine, 2-chloro-4-methyl-3'-hydroxydiphenylamine and 2-chloro-4'-methoxy-3-hydroxydiphenylamine.
• the process according to the invention can be carried out in water and/or a solvent or diluent, the weight ratio of water to solvent or diluent in a water/solvent mixture or water/diluent mixture being about 0.05 to 50, preferably 0.1 to 5.
• Solvents or diluents which can be used are high-boiling phenol ethers with up to 20, preferably 12, carbon atoms. Examples which may be mentioned are: diphenyl ether, methyl phenyl ether, ethyl phenyl ether, propyl phenyl ether and butyl phenyl ether.
• Cyclic sulphones can be mentioned as further solvents or diluents which can be employed within the scope of the process according to the invention, for example tetramethylene sulphone (sulpholane), pentamethylene sulphone, 2-methyl-tetramethylene sulphone and hexamethylene sulphone.
• solvents or diluents are tertiary amines with up to 20 carbon atoms, preferably up to 12 carbon atoms, such as N,N-dimethylaniline, N,N-dethylaniline and N,N-dipropylaniline.
• Possible bases which can be employed within the scope of the process according to the invention are the hydroxides, carbonates, alcoholates, phenolates and/or bicarbonates of the elements of the first and/or second main group of the periodic system and/or the salts of amines and/or of amides of aliphatic and/or aromatic carboxylic acids with up to 12 carbon atoms, which are derived from the elements of the first and/or second main group of the periodic system.
• Examples which may be mentioned of elements of the first and/or second main group of the periodic system are: lithium, sodium, potassium, magnesium and calcium.
• Possible alcoholates are those with up to 12 carbon atoms, preferably up to 5 carbon atoms, such as methylate, ethylate, propylate, butylate and amylate.
• Suitable amines which may be mentioned are aliphatic or aromatic amines with up to 12 carbon atoms, preferably up to 8 carbon atoms, such as dimethylamine, ethylamine, aniline and N-methylaniline.
• Suitable amides which may be mentioned are amides of aromatic or aliphatic carboxylic acids with up to 12 carbon atoms, preferably with up to 6 carbon atoms, such as acetic acid amide, propionic acid amide and benzoic acid amide.
• Particularly suitable bases for the process according to the invention are the hydroxides and/or alcoholates of the elements of the first and/or second main group of the periodic system, the sodium compounds being particularly advantageous.
• the bases can be employed either individually or in mixtures with one another.
• the mixing ratio of the bases with one another is not critical here.
• the bases are employed in 0.1 to 10 times the molar amount, preferably in 1 to 5 times the molar amount, relative to the molar amount of the diphenylamine compounds.
• the process according to the invention can be carried out at a reaction temperature of about 150° to 400° C., preferably of about 210° to 350° C.
• the process according to the invention can be carried out discontinuously and continuously.
• the 2-hydroxycarbazoles prepared by the process according to the invention are valuable intermediate products for dyestuffs (German Reichspatent No. 551,880).

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Indole Compounds (AREA)
• Steroid Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

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ID=6004026

Family Applications (1)

Country Status (7)

Families Citing this family (2)

• 1977
  • 1977-03-18 DE DE2711943A patent/DE2711943C3/de not_active Expired
• 1978
  • 1978-03-06 US US05/883,980 patent/US4137238A/en not_active Expired - Lifetime
  • 1978-03-14 GB GB10040/78A patent/GB1601513A/en not_active Expired
  • 1978-03-15 CH CH282678A patent/CH631442A5/de not_active IP Right Cessation
  • 1978-03-16 JP JP2936278A patent/JPS53116370A/ja active Granted
  • 1978-03-17 FR FR7807843A patent/FR2383926A1/fr active Granted
  • 1978-03-17 BE BE2056770A patent/BE864996A/xx not_active IP Right Cessation

Non-Patent Citations (1)

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